JPH08502964A - 実質的に非晶質ポリエステルの解重合 - Google Patents
実質的に非晶質ポリエステルの解重合Info
- Publication number
- JPH08502964A JPH08502964A JP6511117A JP51111794A JPH08502964A JP H08502964 A JPH08502964 A JP H08502964A JP 6511117 A JP6511117 A JP 6511117A JP 51111794 A JP51111794 A JP 51111794A JP H08502964 A JPH08502964 A JP H08502964A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxide
- amorphous polyester
- substantially amorphous
- mixture
- glycol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 53
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 21
- -1 methanol Chemical compound 0.000 claims abstract description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 60
- 239000003880 polar aprotic solvent Substances 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 13
- 150000001298 alcohols Chemical class 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 10
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 10
- 238000010791 quenching Methods 0.000 claims description 9
- 230000000171 quenching effect Effects 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 4
- 230000007062 hydrolysis Effects 0.000 description 36
- 238000006460 hydrolysis reaction Methods 0.000 description 36
- 239000008188 pellet Substances 0.000 description 32
- 229920000642 polymer Polymers 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 239000002253 acid Substances 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 8
- 150000004679 hydroxides Chemical class 0.000 description 8
- 230000007423 decrease Effects 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 229920008790 Amorphous Polyethylene terephthalate Polymers 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
- VQMIUUBKKPIDBN-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexane-1-carboxylic acid Chemical compound OCC1CCC(C(O)=O)CC1 VQMIUUBKKPIDBN-UHFFFAOYSA-N 0.000 description 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
- KIPZKLNTLVWHAH-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-(2-methyl-3-bicyclo[2.2.1]heptanyl)methyl]phenol Chemical compound CC1C(C2)CCC2C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 KIPZKLNTLVWHAH-UHFFFAOYSA-N 0.000 description 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
- RQMVDDYXNYUIFY-UHFFFAOYSA-N 4-[3-bicyclo[2.2.1]heptanyl-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1C(C2)CCC2C1 RQMVDDYXNYUIFY-UHFFFAOYSA-N 0.000 description 1
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- GVTDRUXHMYZTFF-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-1,4-diol Chemical compound C1CCCC2=C1C(O)=CC=C2O GVTDRUXHMYZTFF-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- DUOYZBNVXGTSRU-UHFFFAOYSA-N acetic acid;benzene-1,3-diol Chemical compound CC(O)=O.CC(O)=O.OC1=CC=CC(O)=C1 DUOYZBNVXGTSRU-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 description 1
- SZCGBFUWBCDIEA-UHFFFAOYSA-N dodecanedial Chemical compound O=CCCCCCCCCCCC=O SZCGBFUWBCDIEA-UHFFFAOYSA-N 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- OPPAMCXEVPUKEF-UHFFFAOYSA-M sodium;3-(3,5-dicarboxyphenoxy)propane-1-sulfonate Chemical compound [Na+].OC(=O)C1=CC(OCCCS([O-])(=O)=O)=CC(C(O)=O)=C1 OPPAMCXEVPUKEF-UHFFFAOYSA-M 0.000 description 1
- VLKQLHFSNPYQRX-UHFFFAOYSA-M sodium;3-carboxy-5-(4-sulfophenoxy)benzoate Chemical compound OC(=O)C1=CC(C(=O)O)=CC(OC=2C=CC(=CC=2)S(=O)(=O)O[Na])=C1 VLKQLHFSNPYQRX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Sustainable Development (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/970,220 US5328982A (en) | 1992-11-02 | 1992-11-02 | Depolymerization of substantially amorphous polyesters |
| US970,220 | 1992-11-02 | ||
| PCT/US1993/009928 WO1994010121A1 (en) | 1992-11-02 | 1993-10-19 | Depolymerization of substantially amorphous polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08502964A true JPH08502964A (ja) | 1996-04-02 |
Family
ID=25516605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6511117A Pending JPH08502964A (ja) | 1992-11-02 | 1993-10-19 | 実質的に非晶質ポリエステルの解重合 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5328982A (de) |
| EP (1) | EP0666837B1 (de) |
| JP (1) | JPH08502964A (de) |
| KR (1) | KR950704225A (de) |
| AT (1) | ATE147061T1 (de) |
| CA (1) | CA2145747A1 (de) |
| DE (1) | DE69307152T2 (de) |
| ES (1) | ES2096338T3 (de) |
| WO (1) | WO1994010121A1 (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023541162A (ja) * | 2020-09-18 | 2023-09-28 | コリア リサーチ インスティチュート オブ ケミカル テクノロジー | エステル官能基を含む高分子の解重合触媒及びそれを用いた解重合方法 |
| JPWO2025192196A1 (de) * | 2024-03-15 | 2025-09-18 | ||
| WO2025192195A1 (ja) * | 2024-03-15 | 2025-09-18 | 東洋製罐グループホールディングス株式会社 | ポリエステル解重合用薬液、及びポリエステルの解重合方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5414113A (en) * | 1993-10-18 | 1995-05-09 | Amoco Corporation | Process for recovery of aromatic acid from waste polyester resin |
| CA2159412A1 (en) * | 1994-11-04 | 1996-05-05 | H. Clay Linstid Iii | Process for reducing black specks in a thermotropic liquid crystal polymer |
| US6147129A (en) * | 1998-10-01 | 2000-11-14 | The Coca-Cola Company | Method for treating polyesters and, in particular, cleaning and decontaminating polyesters |
| WO2001036523A1 (de) * | 1999-11-18 | 2001-05-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur wiedergewinnung von polyestern oder polyestergemischen |
| CZ2000969A3 (cs) * | 2000-03-17 | 2001-08-15 | Milan Ing. Šírek | Způsob chemické recyklace odpadního polyethylentereftalátu |
| US7098299B1 (en) * | 2005-03-16 | 2006-08-29 | United Resource Recovery Corporation | Separation of contaminants from polyester materials |
| WO2007029728A1 (ja) * | 2005-09-06 | 2007-03-15 | Unitika Ltd. | ポリエステル樹脂水性分散体、それから得られる被膜、および該被膜を利用した包装袋 |
| US9458354B2 (en) | 2010-10-06 | 2016-10-04 | Resinate Technologies, Inc. | Polyurethane dispersions and methods of making and using same |
| CN103703086A (zh) | 2011-06-10 | 2014-04-02 | 克里斯托弗·M·费利斯 | 透明涂层，丙烯酸类涂层 |
| US9732026B2 (en) | 2012-12-14 | 2017-08-15 | Resinate Technologies, Inc. | Reaction products containing hydroxyalkylterephthalates and methods of making and using same |
| US9550713B1 (en) | 2015-07-09 | 2017-01-24 | Loop Industries, Inc. | Polyethylene terephthalate depolymerization |
| MX2018014090A (es) | 2016-05-19 | 2019-04-01 | Carbios | Un proceso para degradar productos de plastico. |
| US10808096B2 (en) | 2018-06-25 | 2020-10-20 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| US12071519B2 (en) | 2017-09-15 | 2024-08-27 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| US10252976B1 (en) | 2017-09-15 | 2019-04-09 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| DE102018209567A1 (de) * | 2018-06-14 | 2019-12-19 | Rampf Holding Gmbh & Co. Kg | Verfahren zum Abbau von Kunststoffen |
| DE102018122210B4 (de) | 2018-09-12 | 2023-06-29 | Rittec Umwelttechnik Gmbh | Verfahren und Verwendung einer Vorrichtung zur Wiederaufarbeitung von Polyalkylenterephthalat enthaltenden Abfällen |
| US11248103B2 (en) | 2019-03-20 | 2022-02-15 | 9449710 Canada Inc. | Process for the depolymerization of polyethylene terephthalate (PET) |
| EP3907250A1 (de) * | 2020-05-06 | 2021-11-10 | Universitaet Konstanz | Polyester or polycarbonat-artige materialien, ihre solvolyse und herstellung von fertigteilen daraus |
| WO2025052233A1 (en) * | 2023-09-05 | 2025-03-13 | Università Degli Studi Di Milano | Recycling process of polyesters from mixed plastic waste |
| CN117990821B (zh) * | 2024-01-09 | 2024-12-10 | 上海新泊地化工技术服务有限公司 | 一种适用于液晶聚合物聚合单体结构分析的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1061772B (de) * | 1957-02-08 | 1959-07-23 | Rhodiaceta | Verfahren zur Herstellung von Terephthalsaeure durch Abbau von Polymethylenterephthalaten |
| US3952053A (en) * | 1974-02-26 | 1976-04-20 | Safetech, Inc. | Method for recovering terephthalic acid and ethylene glycol from polyester materials |
| OA05495A (fr) * | 1975-12-16 | 1981-04-30 | Rhone Poulenc Textile | Procédé d'obtention de TEREPHTALATE de DIMETHYLE à partir de déchets de polyester. |
| US4078143A (en) * | 1976-01-09 | 1978-03-07 | E. I. Du Pont De Nemours And Company | Process for depolymerizing waste ethylene terephthalate polyester |
| US4355175A (en) * | 1981-04-06 | 1982-10-19 | Pusztaszeri Stephen F | Method for recovery of terephthalic acid from polyester scrap |
| US4542239A (en) * | 1981-11-18 | 1985-09-17 | Board Of Control Of Michigan Technological University | Process for recovering terephthalic acid from waste polyethylene terephthalate |
| US4605762A (en) * | 1982-04-23 | 1986-08-12 | Celanese Mexicana S.A. | Depolymerization of condensation polymers |
| US4620032A (en) * | 1984-12-11 | 1986-10-28 | Celanese Corporation | Depolymerization of condensation polymers involving a pre-molecular weight reduction step |
| US4578502A (en) * | 1985-01-22 | 1986-03-25 | Cudmore Warner J G | Polyethylene terephthalate saponification process |
| US4876378A (en) * | 1988-05-23 | 1989-10-24 | Eastman Kodak Company | Recovery of dialkyl naphthalene-2,6-dicarboxylates from naphthalene-2,6-dicarboxylic acid-containing polyesters |
| US5045122A (en) * | 1989-12-14 | 1991-09-03 | Eastman Kodak Company | Ester hydrolysis and depolymerization of polyester and polycarbonate polymers |
-
1992
- 1992-11-02 US US07/970,220 patent/US5328982A/en not_active Expired - Fee Related
-
1993
- 1993-10-19 CA CA002145747A patent/CA2145747A1/en not_active Abandoned
- 1993-10-19 EP EP93923922A patent/EP0666837B1/de not_active Expired - Lifetime
- 1993-10-19 JP JP6511117A patent/JPH08502964A/ja active Pending
- 1993-10-19 ES ES93923922T patent/ES2096338T3/es not_active Expired - Lifetime
- 1993-10-19 WO PCT/US1993/009928 patent/WO1994010121A1/en not_active Ceased
- 1993-10-19 DE DE69307152T patent/DE69307152T2/de not_active Expired - Fee Related
- 1993-10-19 KR KR1019950701731A patent/KR950704225A/ko not_active Abandoned
- 1993-10-19 AT AT93923922T patent/ATE147061T1/de not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023541162A (ja) * | 2020-09-18 | 2023-09-28 | コリア リサーチ インスティチュート オブ ケミカル テクノロジー | エステル官能基を含む高分子の解重合触媒及びそれを用いた解重合方法 |
| JPWO2025192196A1 (de) * | 2024-03-15 | 2025-09-18 | ||
| WO2025192195A1 (ja) * | 2024-03-15 | 2025-09-18 | 東洋製罐グループホールディングス株式会社 | ポリエステル解重合用薬液、及びポリエステルの解重合方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR950704225A (ko) | 1995-11-17 |
| US5328982A (en) | 1994-07-12 |
| DE69307152D1 (de) | 1997-02-13 |
| EP0666837A1 (de) | 1995-08-16 |
| ATE147061T1 (de) | 1997-01-15 |
| DE69307152T2 (de) | 1997-04-24 |
| EP0666837B1 (de) | 1997-01-02 |
| WO1994010121A1 (en) | 1994-05-11 |
| ES2096338T3 (es) | 1997-03-01 |
| CA2145747A1 (en) | 1994-05-11 |
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